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Structural variation and (+)-amphetamine-like discriminative stimulus properties.

R Oberlender1, D E Nichols

  • 1Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907.

Pharmacology, Biochemistry, and Behavior
|March 1, 1991
PubMed
Summary
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Researchers studied amphetamine structure variations in rats. Specific molecular changes, like those in 2-amino-1,2-dihydronaphthalene, mimicked amphetamine

Area of Science:

  • Pharmacology
  • Neuroscience
  • Medicinal Chemistry

Background:

  • (+)-Amphetamine sulfate is a central nervous system stimulant.
  • Drug discrimination paradigms are used to understand the stimulus effects of psychoactive drugs.
  • Structure-activity relationships help elucidate the molecular requirements for drug action.

Purpose of the Study:

  • To investigate how modifications to the amphetamine molecular structure affect its discriminative stimulus properties.
  • To identify key structural features responsible for the central nervous system stimulant effects of amphetamine.

Main Methods:

  • Rats were trained to discriminate (+)-amphetamine sulfate from saline in a two-lever, food-reinforced task.
  • Various amphetamine analogues with side chain variations were administered.

Related Experiment Videos

  • Generalization patterns and relative potencies were analyzed to assess stimulus equivalence.

    • Main Results:

    • Partial generalization to (+)-AEPEA and 2-aminoindan (AI) was observed.
    • 2-amino-1,2-dihydronaphthalene (ADN) and 2-aminotetralin (AT) fully substituted for (+)-amphetamine.
    • ADN was 1/4 as potent and AT was 1/8 as potent as (+)-amphetamine; the S-(-)-isomer of ADN mediated this effect.
    • 5,6-methylenedioxy-2-aminoindan (MDAI) did not substitute for (+)-amphetamine.

    Conclusions:

    • Constraining or extending the alpha-alkyl substituent of amphetamine reduces its ability to produce amphetamine-like discriminative stimulus effects.
    • Specific structural modifications, such as those in ADN and AT, can retain or mimic the discriminative properties of amphetamine.
    • The stereochemistry of substituents plays a crucial role in the pharmacological activity of amphetamine analogues.